


Labor Day Travels

by alishadow



Category: How to Get Away with Murder, Shameless (US)
Genre: Fluff, M/M, Traveling
Language: English
Status: Completed
Published: 2015-09-18
Updated: 2015-09-18
Packaged: 2018-04-21 08:10:57
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,768
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4821710
Author URL: https://archiveofourown.org/users/alishadow/pseuds/alishadow
Summary: <blockquote class="userstuff">
              <p>Connor Walsh decides to take his boyfriend on a trip to Chicago to visit his sister. While on their mini vacation, they bump into a duo who may sound a tad familiar to some of you.</p>
            </blockquote>





	Labor Day Travels

**Author's Note:**

> First of all, i'm aware Connor's sister does not live in Chicago. I desperately wanted to somehow do a crossover of Coliver and Gallavich. The plot to this story popped into my head and i went with it. So yeah, some details are changed in order for this story to make sense. I really hope to create more stories with these two couples in the future, since i wasn't able to add Ian into this particular one. Second of all, because we don't know a ton about Connor's family at this moment in time, i made up all the names. If season two reveals them, i'll be sure to change it. And last but certainly not least, the grammar may not be perfect and i apologize for that. I try my best. Enjoy!

Connor gripped the envelope containing the flight tickets as tightly as he could manage. He was only steps away from his boyfriends apartment door. His nerves intensified once he saw the door that had the numbers reading 303. He took a deep breath and reached towards the door.

A few weeks back, Connor’s sister, Gemma, called him up asking if he could visit her soon. With Connor’s hectic schedule, he didn’t make it out to see Gemma very often. When she was twenty-four, she moved out to Chicago to start a new life for herself. But Connor stayed home to attend Law school. 

Gemma brought up the idea of coming over during Labor Day weekend. She desperately wanted to meet the man who changed her brother’s strict ‘no boyfriend’ policy. She imagined this man must be something special, for she never thought she would she her brother willingly commit to anyone. 

Connor agreed with the idea and bought the plane tickets immediately. He always had a good relationship with Gemma growing up and he was anxious to see her again. The only problem was getting Oliver to agree. He had no idea how he would react to the idea of traveling with Connor. Despite dating for over a year at this point, he was still worried Oliver would reject the idea.

Connor knocked on the door and before he could manage a third pound, Oliver’s smiling face was right in front of him. Connor thought he felt the wind being knocked out of him. 

“Hey,” Oliver said with a huge grin plastered on his face.

“Uh…hi,” Connor said, with the nerves taking full force.

“Come in,” Oliver said while moving out of Connors way. Connor walked towards the couch where Oliver was now sitting.

“Is something wrong?” Oliver asked. He could immeditaley tell something was off about his boyfriend.

“No,” Connor quickly replied. 

“Oh. Well, do you mind me asking what’s in that envelope you’re holding onto for dear life?”

Connor started to grin as he looked down at the paper in his grip. “Um…well…”

Oliver just smiled as Connor jumbled his words together. He loved seeing the softer side of him. Oliver always loved how Connor felt comfortable to open up about personal things going on in his life.

“A few weeks ago I was talking to my sister and she made a suggestion that we…um…go visit her?” 

“The one in Chicago?” Oliver asks, even though he knew Connor only had one sister.

“Yeah. It would just be for the weekend. We’ll be back in time for work on Tuesday.”

“Yeah, that sounds great,” Oliver said with a huge smile.

Connor’s eyes widened as he looked at Oliver. “Really?”

“Of course,” Oliver told him. “You know I’ve always wanted to meet your family. I don’t see why you would ever think I’d reject the idea of meeting someone you’re very close with.”

Connor felt all the worry wash right out of him. “Okay… well, we’ll have to leave tomorrow morning.” He said with much more confidence.

“Sounds perfect. You mind helping me pack?” Oliver asked with a wink. 

Connor immediately caught on to what Oliver was getting at. “Uh, yeah,” he said. They both got up from the couch and spent the rest of the night doing anything else but packing. 

\---

Connor woke up a little bit after seven to prepare breakfast before they headed for the airport. In case Oliver said yes, Connor already packed his suitcase. Luckily, he didn’t waste the twenty minutes it took to do so. 

Eventually, Oliver stumbled into the kitchen. He walked over to Connor and snuck up behind him flipping the pancakes. He slid his arms around Connors waist. He loved to show Connor any sort of affection and Connor secretly loved it as well. 

“My favorite,” Oliver stated as he turned around to get the syrup.

“Of course,” Connor replied as he finished up the last batch of pancakes. They both took a seat at the dining table to quickly eat the food.

“I’m really excited to meet you’re sisters children,” Oliver said as he stuffed his face with the pancakes.

“Yeah, they’re pretty cool for kids and all,” Connor said with a smile. He was in a really great mood today. Maybe it was because he was going to see Gemma. But he was almost positive it was because he would be with Oliver all weekend. 

“Shit!” Oliver stated out of the blue with panic taking over his once calm smile.

“What?” Connor asked, immediately standing up with Oliver.

“I never got around to packing! What do I need? Suits? Swimming trunks?”

“Ollie, I think we’re both in agreement that if we went swimming, the trunks wouldn’t be necessary,” Connor said with his normal smirk.

“Shut up, Connor!” Oliver said as he ran into his room to pack. 

Connor stayed in the kitchen to clean up the tiny mess he made. He heard every cabinet door open in Oliver’s room at least twice. Finally, Oliver made his way out of the room with a suitcase in hand.

Through frantic gasps, Oliver managed to tell Connor he was ready for Chicago. Connor took his hand as they walked out of the apartment building.

\---

The flight wasn’t too long distance wise, but it felt to go on forever for Connor. They ended up watching a few movies on the way. Neither which were a tad bit interesting to Connor. 

Once they landed, Connor felt the nerves start to creep back in. The thought of not only seeing Gemma, but also introducing her to Oliver started to feel awfully surreal. 

“You okay?” Oliver asked as they got into the rental car. 

“Yeah, I’m okay,” Connor said as he started pulling out of the parking spot.

“It’s okay to be nervous,” Oliver told him with a smile. He always knew Connor better than Connor did himself. It scared Connor at first, but he’s gotten used to the idea over time.

The rest of the ride was filled with comfortable silence. The traffic was bad, as expected, but they were content with being able to take in the beautiful scenery. Connor had only visited Gemma in Chicago two other times, so he still wasn’t very familiar with the area. Luckily, he recognized her home once he saw it. The small but cozy brick home was just what Connor and Oliver needed after the long day they had. 

“Are you ready?” Oliver asked Connor while taking his hand in his.

“Of course,” Connor said and stepped out of the car.

\---

Before Connor even had a chance to knock on Gemma's door, he was greeted by his sister’s warm smile.

“Connor!” She said with much enthusiasm, “I can’t believe you actually got your ass down here!”

Connor laughed at his sister’s comment. They always shared the same sense of humor. 

“And this,” she said while looking in Oliver’s direction, “must be one incredible man!”

Oliver slightly blushed while also giving a huge grin. They went in for a hug and Connor smiled to himself. This was going much better than expected.

“I can not tell you how great it is to finally meet the man who made my brother settle. For awhile there I never thought I’d see the damn day!”

“Alright, Gemma...” Connor said through gritted teeth.

“Right! sorry,” she said while still smiling, “let’s head on inside.”

“Nick! Leah! Connor is here! Gemma yelled towards the upstairs part of the house. The sound of pounding footsteps was immediately heard throughout the house. 

“Connor!” they both yelled as they went in for a hug. He knelt down to get on their level.

Oliver smiled as he saw the way he was around the children. He never got the chance to see how Connor was around kids, but seeing his love for them gave him the craving for a child of their own.

“Who’s this?” Nick asked while pointing at Oliver.

“That,” Connor said while standing back up, “is my boyfriend. Oliver.”

“Hi Oliver,” Nick and Leah in synchrony.

“Hello, “Oliver said while waving at them.

“Well, let’s go have some lunch, shall we?” Gemma asked.

“Sounds great,” Connor said while leading Oliver towards the dining table.

\---

Throughout the meal, Connor and Gemma took up most of the conversation. They had a lot more catching up to do than either of them imagined. Of course, Gemma asked plenty about Oliver as well. 

Oliver found it easy to communicate with Gemma. Even though he tried to hide it in front of Connor, he was extremely nervous about meeting his sister's approval. But she immediately treated him like a long time friend. 

Oliver also really enjoyed Leah and Nick’s snide remarks made every once in while throughout conversation. Eventually, the kids got bored and left to play whatever video game they were obsessed with at the moment. 

The conversation between the three of them went on for hours, though. And before any of them realized it, the clock stroke 5pm. 

“Mike should be here any moment, he’s really excited to meet you, Oliver,” Gemma said while taking another gulp of whine.

“Sounds fantastic,” Oliver said with a genuine smile.

\---

The rest of the night was filled with laughter and memories to last everyone a lifetime. Gemma's husband, Mike, was incredibly kind to Oliver. It all felt like a huge family reunion to Oliver, despite never meeting the two before today. 

When the four of them became aware of the late time, they decided to prepare to go their separate ways for the night. Gemma and Mike slept downstairs while the guest room was upstairs.

“Oliver, if you don’t mind, I just want to talk to Connor for a quick minute,” Gemma asked.

“Of course,” Oliver said as he slugged himself up the stairs. He had a few too many glasses of wine to say the least.

“That’s quite the guy you got there, Connor,” Gemma said as she picked the dishes off the table and carried them into the kitchen.

“Yeah, He’s definitely different from the…past guys,” Connor mumbled.

“But he cares, Connor. And I think as much as you hate to admit it, you want a guy who truly cares at the end of the day.”

“Yeah…” Connor mumbled. He knew his sister was probably right.

“Well, I hope it all goes well for you two. He’d make a great dad one day,” she said with a smirk.

“I hate you,” Connor blankly told her, yet still with a tiny smile on his face.

\---

The next morning, Gemma brought Oliver and Connor shopping around Michigan Avenue. They went into almost any store you could imagine, but barely bought a single thing. The experience alone was enough for them.

Even though Connor loved his sister, he really wanted to spend some alone time with Oliver. Gemma eventually caught on to Connor’s wishes and took a taxi back to her home.

“So... I was thinking we could head over to Lincoln Park?" Connor asked Oliver.

“Sounds great. Do you think we could maybe stop for some coffee on our way?” Oliver asked.

“Sure,” Connor complied. He could use some caffeine after dealing with his sister all morning.

\---

“How about this place?” Oliver asked.

The tiny building had a sign that read ‘Milkovich Café’ over the doors.

“Uh…I guess,” Connor said while walking towards the entrance. The place was pretty tiny and only three other people sat in the chairs surrounding the counter.

“This place is adorable! Oliver said with delight. “Do you mind if we stay here for a bit?”

Connor couldn’t say no to a smiling Oliver. “Of course.”

A young girl with black hair was waiting by the cash register. “Hello, I’m Mandy. How may I help you?”

“Uh… we’ll take two medium coffee’s for here, please.”

“Sure thing,” the girl replied and got to working on their orders. 

In almost no time, Mandy had the drinks ready and handed them over to Connor. 

“I can’t believe more people aren’t here,” Oliver told Connor as he came over to the table Oliver picked out. “This place is so cozy.”

Connor nodded in agreement. The store felt very out of place for being in the midst of the crazy life of Chicago. 

All of a sudden, the front door to the building flew open as a young man came storming over to Mandy.

“I’m fucked,” he yelled way too loudly.

Oliver looked over at Connor with confusion, but Connor just shrugged. 

“Shut up, Mickey! We have customers for once,” Mandy told the man, who was short and had dark hair. He took a uniform off a rack and slid it on. 

The girl, Mandy, sighed. “What’s the matter, Mickey?”

“I forgot that Ian’s fucking birthday is today. Who the fuck forgets their boyfriends fucking birthday?”

Connor couldn’t help but let out a laugh.

Mickey’s gaze immediately fell onto Connor. “You got a fucking problem?”

Connor met his gaze hastily. “Nope,” he replied.

“Good. Now take you and your boyfriends ass somewhere else.”

“Mickey!” Mandy yelled while pushing him away from the register. “Sorry about my dick of a brother. Just ignore him.” 

“It’s fine,” Oliver told the nice girl.

“Hello? Mandy? What the fuck do I get him?” Mickey asked with force.

“I don’t know! He’s your boyfriend!”

“And he’s your best friend!” 

Hearing this conversation made Connor reflect on when he asked Ally what to get Oliver in hopes to win him back. Her suggestion was flowers, and even though Connor never had the chance to give him the flowers he bought at that moment in time, he had done it plenty of times since.

“Get him flowers,” Connor said towards Mickey.

Mickey gave a harsh laugh. “Ian would fucking hate flowers.”

“Just trust me on this one,” Connor replied. 

\---

“Thank you so much for taking me here, Connor. It really means a lot to me. Your sister and Mike we’re extremely nice.”

“You’re welcome,” Connor says. After they left the Milkovich Café, they headed off to the park. They’ve been walking around for about an hour at this point. 

“I almost don’t want to head back to Philly,” Oliver confesses. 

“I definitely agree with you on that one,” Connor says.

“Say… maybe once we get back home I could invite my parents over for dinner sometime?” Oliver asks.

“Of course. I guess it’s only natural we do the whole parent thing next.”

“Yeah,” Oliver mumbled. He still couldn’t believe a man like Connor could love him. But each day, he proves just how wrong Oliver is for ever thinking such silly thoughts.

\---

Monday morning finally rolled around, which meant it was finally time to head back to Philadelphia. 

“You better come back soon, Connor,” Gemma said with a stern face. 

“I will. I promise,” Connor said while giving one last hug to his sister.

“You too, Oliver. It was wonderful getting to meet you,” Gemma said with a warm smile.

“As to you,” Oliver said while hugging her back.

The two headed off towards the airport to return back to their hectic lives in Philly.

\---

Once the two boarded the plane, Oliver felt sadness immediately take over his body. He never thought he would go on a vacation with Connor so soon into their relationship. Getting away from the drama of both of their jobs made Oliver feel like the happiest man in the world. For once, Connor and him we’re just a normal couple. 

Oliver thought back to the young boy in the coffee shop started wondering if the kid known as Mickey ever followed through on Connor’s advice.

“I never told you how sweet it was to tell that boy to get his boyfriend some flowers,” Oliver mumbled.

“How was that sweet?” Connor asked.

“Because you’re…well…Connor Walsh.”

“All I know is that you’re a sucker for anything with a petal on it,” Connor replied.

“Not true. I never once asked for a bike.”

“Oh my god,” Connor said as he rolled his eyes. “Don’t ever try to make a joke again,” he said as they both bursted out laughing.

\---

Even though there was still daylight out once they reached Oliver’s apartment, they both headed straight for the bed. They immediately started stripping off the layers of clothes covering their skin and hopped into bed.

“Thank you so much for sharing another part of your life with me,” Oliver said while grinning.

“My pleasure,” Connor said as he pressed a kiss to Oliver’s forehead. And with that, they both fell into a blissful sleep.

 

The End.


End file.
